57260-73-8

Basic information

• Product Name: N-Boc-Ethylenediamine
• Synonyms: (2-AMINO-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER;1-BOC-ETHYLENEDIAMINE;1-BOC-AMINO-1,2-ETHANEDIAMINE;AKOS 91563;BUTTPARK 27\08-29;BOC-EDA;BOC-DIAMINOETHANE;BOC-NH-(CH2)2-NH2
• CAS NO: 57260-73-8
• Molecular Formula: C₇H₁₆N₂O₂
• Molecular Weight: 160.21
• EINECS: 1312995-182-4
• Product Categories: N-BOC;Amines;blocks;Amines and Anilines;Aliphatics;Nitric Oxide Reagents;Exciton Chirality CD Methodfor (for Monofunctional Compounds);Monoprotected Diaminoalkanes;N-Boc-diaminoalkanes;Absolute Configuration Determination (Exciton Chirality CD Method);Analytical Chemistry;Enantiomer Excess & Absolute Configuration Determination;Cross Linking Reagents
• Mol File: 57260-73-8.mol

Chemical Properties

• Boiling Point: 72-80 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to very light yellow/Oily Liquid
• Density: 1.012 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Storage Temp.: Refrigerator (+4°C)
• PKA: 12.40±0.46(Predicted)
• Water Solubility: Miscible with methanol and chloroform. Slightly miscible with water.
• Sensitive: Air Sensitive
• BRN: 1932330
• CAS DataBase Reference: N-Boc-Ethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-Ethylenediamine(57260-73-8)
• EPA Substance Registry System: N-Boc-Ethylenediamine(57260-73-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 57260-73-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-Ethylenediamine is used as a protecting group for amines in the synthesis of various pharmaceutical compounds. It is particularly useful in the development of new drugs and the modification of existing ones, as it helps prevent unwanted side reactions and improves the overall yield of the desired product.
Used in Chemical Synthesis:
N-Boc-Ethylenediamine is used as a reagent in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds in organic chemistry. This reaction is particularly useful in the synthesis of complex organic molecules, such as natural products and pharmaceuticals.
Used in Synthesis of Thyronamine Derivatives:
N-Boc-Ethylenediamine is used in the synthesis of thyronamine derivatives and analogs, which are compounds with potential applications in the treatment of various medical conditions. The use of N-Boc-Ethylenediamine in this context allows for the efficient and selective synthesis of these biologically active molecules.
Used in Oligonucleotide and Peptide Synthesis:
N-Boc-Ethylenediamine is used as a protecting group in the synthesis of oligonucleotides and peptides, which are essential components of genetic material and proteins, respectively. The use of this protecting group helps to prevent unwanted side reactions and ensures the successful formation of the desired sequences.
Used in the Preparation of (2-isothiocyanato-ethyl)-carbamic acid tert-butyl ester:
N-Boc-Ethylenediamine is used in the preparation of (2-isothiocyanato-ethyl)-carbamic acid tert-butyl ester by reacting with carbon disulfide. N-Boc-Ethylenediamine has potential applications in the synthesis of various organic molecules and materials, further demonstrating the versatility of N-Boc-Ethylenediamine in chemical synthesis.

InChI:InChI=1/C7H16N2O2/c1-7(2,3)11-6(10)9-5-4-8/h4-5,8H2,1-3H3,(H,9,10)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 107-15-3 ethylenediamine 
• 322474-21-5 N,N'-bis-Boc-S-methyl-isothiourea 
• 636795-25-0 3-fluoro-4-(4-trifluoromethyl-benzyloxy)-benzoic acid 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 34046-07-6 N-benzyloxycarbonyl-N-(2-t.butoxycarbonylaminoethyl)glycine 
• 137743-46-5 2-tert-butyloxycarbonylaminoethyl isothiocyanate 
• 126813-46-5 N-<2-<<(1-dimethylethoxy)carbonyl>amino>ethyl>-4-chloro-3-nitrobenzenesulfonamide 
• 153802-38-1 [(S)-2-tert-Butoxy-1-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-ethyl]-carbamic acid benzyl ester 
• 77153-07-2 S-methyl-N-<2-<(tert-butoxycarbonyl)amino>ethyl>-N'-tosylisothiourea 
• 92741-56-5 N-<2'-(N''-Z-2-aminoethyl)-2,4'-bithiazole-4-carboxy>-N'-Boc-1,2-diaminoethane 
• 117498-75-6 <4-<<2-<(tert-butoxycarbonyl)amino>ethyl>amino>-3-nitrophenyl>(2-thienyl)methanone 
• 117498-54-1 (4-amino-3-nitrophenyl)<4-<ethyl>carbamoyl>methyl>2-thienyl>methanone 
• 90013-30-2 N²-benzyloxycarbonyl-N⁴-(2-tert-butoxycarbonylaminoethyl)-L-asparagine p-nitrobenzyl ester 
• 117861-32-2 <(β-mercapto-β,β-pentamethylenepropionyl)>D-Tyr(Et)-Phe-Val-Asn-Cys-Pro-NH(CH2)2NH2 
• 144510-94-1 6,9-bis<<2-ethyl>amino>benzoisoquinoline-5,10-dione 
• 154384-92-6 6-<<2-(t-butoxycarbonylamino)ethyl>amino>-9-<(4-methylphenyl)sulfonyloxy>benzophthalazine-5,10-dione 
• 215654-55-0 (Z)-3-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-acrylic acid 
• 58827-18-2 N-(2-aminoethyl)furan-2-ylcarboxamide 

Relevant articles and documents

Formation of a tris(catecholato) iron(iii) complex with a nature-inspired cyclic peptoid ligand

Siderophore-mimicking macrocyclic peptoids were synthesized. Peptoid3with intramolecular hydrogen bonds showed an optimally arranged primary coordination sphere leading to a stable catecholate-iron complex. The tris(catecholato) structure of 3-Fe(iii) was determined with UV-vis, fluorescence, and EPR spectroscopies and DFT calculations. The iron binding affinity was comparable to that of deferoxamine, with enhanced stability upon air exposure.

Flow-mediated synthesis of Boc, Fmoc, and Dd iv monoprotected diamines

A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access to N-Boc-, N-Fmoc-, and N-Ddiv-protected compounds with productivity indexes of 1.2-3.6 g/h.

An inorganic phosphate (Pi) sensor triggers 'turn-on' fluorescence response by removal of a Cu2+ ion from a Cu 2+-ligand sensor: Determination of Pi in biological samples

A fluorescent ligand that displays a high selectivity for Cu2+ has been synthesized. On complexation with Cu2+, the fluorescence of the ligand is quenched. Inorganic phosphate ions decomplex Cu2+ displaying a fluorescence enhancement that can even be seen with naked eyes. The method was successfully used in quantitative determination of inorganic phosphates in serum, urine, and saliva samples.

An optimised synthesis of 2-[2,3-Bis(tert -butoxycarbonyl)guanidino] ethylamine

This short report describes an improved, reliable, and high-yielding (>90%) synthesis of 2-[2,3-bis(tert-butoxycarbonyl)guanidino]ethylamine. The method is scalable (>5 g), and the product obtained directly from the reaction mixture requires no further purification. In addition, this methodology can be successfully applied to other diamine substrates (1,3-propyl and 1,4-butyl; 70% and 61% yield, respectively).

Synthesis and photoluminescence study of di-dendron dendrimers derived from mono-Boc-protected ethylenediamine cores

This work is focused on the synthesis and optical properties of cone-shaped structural feature di-dendron polyamidoamine dendrimers up to the third generation with mono-Boc-protected ethylenediamine (EDA) as a core. Strong UV absorbance spectra and fluorescence spectra from di-dendron dendrimers with different terminal groups (-NH2, -COOCH3) were studied under different conditions by varying experimental parameters such as concentration and pH. The optical density and fluorescence intensities increased when di-dendron dendrimers generation number increased from 0.5 to 3.0. It was confirmed that the concentration of di-dendron dendrimers plays an important role in fluorescence intensity. The increase in fluorescence intensity was linear in low concentration regions, but the intensity increased slowly in high concentration regions. The results also showed a rapid increase in fluorescence intensity at low pH. The formation of a fluorescence-emitting moiety had a close relationship to protonated tertiary amine groups in di-dendron dendrimers derived from mono-Boc-protected EDA cores. Furthermore, the formation of fluorescent chemical species was irreversible. Copyright

A fluorescent polymeric heparin sensor

Linear copolymers have been developed which carry binding sites tailored for sulfated sugars. All binding monomers are based on the methacrylamide skeleton and ensure statistical radical copolymerization. They are decorated with o-aminomethylphenylboronates for covalent ester formation and/ or alkylammonium ions for noncovalent Coulomb attraction. Alcohol sidechains maintain a high water solubility; a dansyl monomer was constructed as a fluorescence label. Statistical copoly merization of comonomer mixtures with optimized ratios was started by AIBN (AIBN = 2,2′-azoisobutyronitrile) and furnished water-soluble comonomers with an exceptionally high affinity for glucosaminoglucans. Heparin can be quantitatively detected with an unprecedented 30 nM sensitivity, and a neutral polymer without any ammonium cation is still able to bind the target with almost micromolar affinity. From this unexpected result, we propose a new binding scheme between the boronate and a sulfated ethylene glycol or aminoethanol unit. Although the mechanism of heparin binding involves covalent boronate ester formation, it can be completely reversed by protamine addition, similar to heparin's complex formation with antithrombin III.

Synthesis of ATRP-induced dextran-b-polystyrene diblock copolymers and preliminary investigation of their self-assembly in water

Dextran-b-polystyrene diblock copolymers forming miscellaneous spherical self-assemblies in water were obtained by chemical modification of the anomeric extremity of a commercial dextran followed by atom transfer radical polymerisation of styrene. The Royal Society of Chemistry.

Metal-assisted assembly and stabilization of collagen-like triple helices

Single-chain and TRIS-assembled collagen mimetic peptide structures incorporating catechol groups were synthesized. When 1/3 equiv of Fe3+ was added to the single-chain compound in 50 mM CAPS buffer (pH 10), the 1:3 Fe3+-catechol complex that formed acted as an N-terminal scaffold to assemble the triple helix. When 1 equiv of Fe3+ was added to the TRIS-assembled compound in the buffer solution, the Fe3+-catechol complex acted as an extra C-terminal scaffold, which lead to a triple helix with both termini tethered. The formation of this C-terminal complex increased the Tm by a remarkable 22 °C! Copyright

Fluorobenzamides and uses thereof

The invention relates to fluorobenzamide derivatives of the formula wherein R1, R2, R3 R4, R5, R6 and R7 are as defined herein. =, The compounds of the invention are selective monoamine oxidase B inhibitors and therefore they are suitable for the treatment of diseases mediated by monoamine oxidase B, such as Alzheimer's disease or senile dementia.

Solid-phase synthesis of oligourea peptidomimetics

A procedure for the solid-phase synthesis of oligourea peptidomimetics starting from Boc-protected monomers is described. The compounds are prepared on Tentagel resin and can be obtained selectively rather as the C-terminal free acids with UV irradiation